What are the effects of resonance on acidity in phenols?
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An energy diagram showing the effect of resonance on cyclohexanol and phenol acidities is shown on the right. Since the resonance stabilization of the phenolate conjugate base is much greater than the stabilization of phenol itself, the acidity of phenol relative to cyclohexanol is increased.
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There is no resonance stabilization in the ethoxide ion. Resonance stabilizes both phenol and phenoxide ion by delocalization of electrons into the ring. ... Thus, phenol is 107 times as acidic as ethanol because resonance stabilizes the phenoxide ion.
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